Jensen Karp Talks Hip-Hop and Underestimating Some Young Rapper Named Kanye West

A way-too-nerdy conversation with the author of Kanye West Owes Me $300.

In 1999, Jensen Karp was just another hip-hop-obsessed Jewish kid from the suburbs. That all changed when he called into Los Angeles’s Power 106 to compete on Roll Call, the station’s daily on-air battle segment. After blurting out that his name was “Hot Karl”—an unmentionable sex act you can look up on the Internet—Karp won. He called back the next day and won. In fact, Hot Karl didn’t lose for 45 days, at which point he retired from competition, signed to Interscope, and started his improbable career as a major label rapper.

Karp’s Kanye West Owes Me $300 tells the story of Hot Karl, from his earliest love for the music to the years he spent rubbing shoulders with West and other hip-hop luminaries and his abrupt fall from grace. It’s a funny, irreverent, and always painfully self-aware look back at a bittersweet chapter for Karp, now a comedy writer and co-owner of LA’s Gallery 1988. There’s plenty of juicy anecdotes, celebrity gossip, and shady industry dealings. But ultimately, Kanye West Owes Me $300 is a book about a very specific moment in hip-hop, and how Karp—as much of a fan as he was an artist—found himself in the thick of it.

GQ: My editor told me “make this as nerdy as possible and we’ll dial it back.” So my first question: As an up-and-coming rapper in Los Angeles, did you ever go to the Good Life(1)?Jensen Karp: I definitely went but was too afraid to ever participate. I remember seeing Medusa perform, who was terrifying as a battler. I never really wanted to go up against her. And I was a huge Freestyle Fellowship dude and I knew I could see them if I went. But I was definitely a wallflower, especially since during its salad days I was too young to really hold my own.

(1) The Good Life was a health food store and cafe that hosted experimental, jazz-influenced open mics throughout the nineties.

I did wonder why there was so little mention of underground hip-hop in the book.
The backpack scene never really accepted me. And once they did, basically after my struggles, it was kinda too late. I got along with The High & Mighty, R.A. the Rugged Man, and that’s about it. Mostly just because I was such a new voice for everyone. They liked me and understood that I knew my shit, but I was basically doing what everyone was afraid to do: be themselves.

But that was the world you were coming out of.
At my core. When I started rapping, my only influences were underground. That was literally all I listened to. If you listen to my Roll Call appearances, they are one-hundred percent an underground dude battling. But when they put you in a studio and you’re making songs with Mya and Redman, it’s sort of a dumb move to just keep trying to stunt and get in your Rawkus inspiration. Sometimes I felt forced by the label but other times it was my own expectations. I wish I’d stuck to my guns a little more, not because it would’ve helped me succeed, but just so I could be a little more proud of the failure.

Was this something you and Kanye had in common?
I guess. He was definitely excited to work with Beanie [Sigel], but yeah, he seemed more comfortable talking about Talib. I think the actual backpack he wore was a little corny and didn’t necessarily reflect him (2). I mean, he wasn’t going to Project Blowed (3) or listening to anyone on Def Jux, if that’s what you mean. I had way more underground conversations with Just Blaze than I did Kanye. I don’t think Kanye knew the Molemen (4). I mean he knew Crucial Conflict (5). If they were on the radio, that was more his thing.

(2) Underground rap was referred to, somewhat pejoratively, as “backpack rap” because that was part of the uniform.

(3) Project Blowed is the open-mic event/crew/record label that grew out of the Good Life scene.

(4) The Molemen were a crew of Chicago producers whose releases featured a wide array of indie rappers.

(5) You may remember Chicago’s Crucial Conflict from their 1996 hit “Hay”.

You talk about being one of many people who underestimated him.
I just kept wondering “Why does he want to fuck up the production thing he has going?” He wasn’t even introduced by his own managers as a rapper. There weren’t many rapper/producer hybrids and I think that’s what a lot of people were hung up on that. And he just had so much energy. Other rappers would play their music, bob their head and check their two-way, this dude was standing up and dancing along, looking for people’s reactions and yelling “YOU GET THAT LINE?” It was weird. And I think people were just caught off-guard at the producer with adult braces being so confident and the rapping not being “great.” He got better.

When you signed with Interscope, did you think of it as going pop?
That was a dichotomy that I immediately knew existed. The million-dollar record deal wasn’t being offered to Apathy, or Haystack, or Slug. They were getting offers and flown everywhere, but everyone knew there was a suburban attraction to my music and my look. I think it was something new and with Eminem popping, it was easy to find my formula. I thought I could find a medium ground as a punchline rapper, but yeah, I definitely converted a bit. I both regret that and know it was impossible to avoid when you have a song with Sugar Ray.

"Other rappers would play their music, bob their head and check their two-way, this dude [Kanye] was standing up and dancing along, looking for people’s reactions and yelling “YOU GET THAT LINE?” It was weird."

Mark McGrath is one of those people who just sort of pops up in the book.
I always saw myself as a hip-hop Zelig. So while I wanted to tell this story that I went through, one that has emotion and actual artistic struggle, I could also keep people’s attention because Mack 10 came to my parents house, an A-list celebrity gave me eye infections after making out and Mark McGrath threw me a birthday party.

You spent a lot of time recording at Baseline Studios at the same time as Jay Z. Another rap nerd question: Does that mean you were around Beanie Sigel and Freeway?
Not a bunch, but I knew they were in and out all the time. Kanye once took me to a Jay Z tour rehearsal, which I weirdly left out of the book. But I was Kanye’s guest to just watch them rehearse. So I sat there with Kanye and met Beanie and Freeway and dudes that honestly, weren’t all that excited to see [Kanye] there. We just sat there, then we went to Jay’s birthday party down the street at Chelsea Piers. That’s where Kanye forced himself on to the step and repeat to throw up the Roc sign. That was his whole goal. It was surreal to watch him that night. I would see Ludacris, Just Blaze, Clue, Duro, and the Young Gunz a lot [at Baseline]. It was so creative there. And once Petey Pablo. I laughed at his name.

Throughout the book, there are rumors that Interscope was stockpiling white rappers to take out any competition to Eminem (6). But as you point out, today white rappers barely even register as a novelty. Maybe Jimmy Iovine was just also ahead of his time?
I think Jimmy thought it could work. That’s why he gave me so much. I do think in the back of his mind, especially as he had similar meetings with Apathy and Slug (and a guy who wrote in during my AMA on Reddit), he was stockpiling a bit and hedging his bets. And I think when it stopped making sense to put out competition from within the label, well then the game plan changed. And that makes sense to 36 year-old me, but not to 21 year-old me.

(6) Eminem has spent his career under the Interscope umbrella with Aftermath/Shady Recors

By the end, did you even enjoy rapping anymore? When did the dream really die?
The dream died when I walked out of Jimmy’s [Iovine’s] office. I tried to find other jobs, shit outside of music. I opened the gallery around the same time but that didn’t start to make money for three years. In that meantime, I was drowning. I don’t know why I left it out of book but I sold guitars at a local swap meet. I had some deal about getting display guitars cheap so I’d buy them and sell them on weekends. So when a dude offered me $5,000 to rap again, although every ounce of my body said “no”, I basically had to do it. But ninety-percent of that experience physically hurt me.

Do you think history has vindicated Hot Karl?
It’s been so weird to hear people saying they like the music now. Maybe I’m more open to hearing it? I think they are way more used to my voice in hip-hop. I’m no longer the only one. Also, Eminem got shitty, which is something no one could’ve predicted. Action Bronson sounds just like Ghostface and no one cares at all. It’s just a different time in hip-hop.